While walking through Springfield, Bart and Lisa childishly squabble over who is "gay for Moleman" - fighting, they roll into Professor Frink's basement. He welcomes them, saying that his new astrology machine told him they would come to his house, and he goes on to show them a film of how life will be in their final days of high school, eight years in the future.

Bart and Lisa are graduating. Lisa is doing this two years early, and is bound for Yale. She goes to the prom with a muscular, emotional Milhouse, having only agreed to this after he saved her from a house fire that he caused. Bart is in love with a blond girl, Jenda; after the prom, Bart proposes to Jenda, but she turns him down and ends their relationship, because she doesn't believe he can provide for her.

Meanwhile, Marge has separated from Homer after he blew the family savings on an underwater house. Homer takes Bart to a night on the town in his hover-car, as Donald Fagen’s "I.G.Y. (What a Beatuiful World)" plays in the background, but the only girls they find are Mrs. Krabappel and Ms. Hoover. Bart then decides to get a job at the Kwik-E-Mart. While making a delivery to Mr. Burns, he is held at gunpoint by Snake (who now uses a combination phaser/cellphone), but Bart saves Burns when Snake is distracted by a phone call.

As a reward, Burns offers to send Bart to Yale with his scholarship, which was previously promised to Lisa. Believing it will impress Jenda enough to take him back, Bart accepts. When Lisa finds out at their graduation, she becomes furious with Bart. Meanwhile, in the audience, Homer fights Krusty, whom Marge is now dating.

Jenda does indeed take Bart back, now that he has the scholarship. Meanwhile Lisa, dejected, decides to settle for Milhouse. While walking with Jenda, Bart finds Professor Frink's house, and uses the astrology machine to see what the post-2013 future holds for Lisa and Milhouse: they live a nowhere marriage and Milhouse sells all his bone marrow just to pay the electric bill, which still isn't enough. Bart rushes away to save Lisa from life with Milhouse, and gives her the scholarship.

Jenda dumps Bart again, and he decides he wants a girl who loves him for himself. In the present, Frink tells Bart he will find that special girl... one minute before he dies at the age of 83. Meanwhile, Homer has won back Marge's heart by getting beaten up by Krusty.

The episode was nominated for a 2005 Emmy for Outstanding Animated Program (for Programming Less Than One Hour), withFamily Guy's "North by North Quahog",South Park's "Best Friends Forever"SpongeBob SquarePants' "Fear of a Krabby Patty".The winning episode was South Park.